
5376 SHADOW LAWN DRIVE, SARASOTA, FL, 34242
Active16 days on marketListed Oct 22, 2026MLS #A4707331
About this home
5376 SHADOW LAWN DRIVE
Some homes on Siesta Key are about the beach. Others are about boating. This one lets you have both. Set along a protected canal with direct boating access to Sarasota Bay through the Grand Canal, and from there to the Intracoastal Waterway and the Gulf, this Siesta Key waterfront home is made for the way life is meant to be lived. Take the boat out for the morning, launch a kayak or paddleboard from your own waterfront, spend some time at Siesta Key Beach, then come home to your private saltwater pool, outdoor kitchen and quiet canal view. The important updates are already here too: a 2021 reroof, impact windows and sliders installed in 2022, plus new first floor flooring, fresh interior paint, a luxury renovation of the first floor primary bath, an outdoor kitchen and waterfront pavers, all completed in 2026. Plantation shutters finish every window and slider. At the center of the home, a fully screened courtyard lanai with a tabletop fire pit extends the living space. Seven impact sliders connect several rooms directly to the courtyard, filling the home with natural light and creating an easy indoor outdoor flow toward the pool and waterfront. Additional sliders from the flex room open toward the pool. The home and pool sustained no storm damage during the 2024 storms. If you haven’t dropped anchor yet, wait until you see the two amazing primary suites. The first floor primary offers courtyard access, two walk in closets and a beautifully renovated 2026 ensuite bath with upscale finishes. Upstairs, the entire second level becomes a private retreat with canal views, a spacious bath, two more walk in closets and its own waterfront balcony. One closet is so large you may wonder if it could qualify as a New York City apartment. When it is time for a little quiet, open the sliders and take in sunset over the canal, or start your morning with fresh air and coffee on the balcony. A redesigned media and flex area now includes an additional bedroom while preserving an approximately 424 square foot flex room for a media room, gym, game room or lounge. Another bedroom includes a Murphy bed and built in desk, making it an easy guest room, home office or both. Outside is where this home really earns its Siesta Key address. The private saltwater pool is surrounded by tropical landscaping and spaces for relaxing, dining and entertaining. The seawall, bulkhead and davits were replaced in 2021, with the waterfront setup planned around a 45 foot Sea Ray. This is a home for boaters who want to use the water, not simply look at it. Set in the heart of Siesta Key, the home is just minutes from Siesta Key Beach, named the No. 1 in the U.S. for 2026 and recognized among the nation’s best many times over. Known for its powdery quartz sand and Gulf waters, it is one of the reasons living here is so special. Siesta Key Village is close by for restaurants, bars, live music and boutiques. Sarasota is just beyond the North Bridge, with downtown waterfront dining, shopping, galleries, theaters, performing arts and cultural attractions close at hand. Whether you are looking for a full time Siesta Key waterfront home or a second home for family and friends, 5376 Shadow Lawn Drive offers true boating access, a private saltwater pool, substantial updates, flexible living space and an exceptional island location. This is the kind of home where every day can include the beach, the boat and dinner by the pool. That is a pretty wonderful way to live.
Facts & features
The home at a glance
5
Bedrooms
4.5
Bathrooms
3,721
Sqft
0.32 ac
Lot size
2
Garage
1964
Year built
Two
Levels
$645
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$17,095 /mo · 10% down Conventional, 30-yr fixed at 7.5%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$17,095/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−1.1%
$/sqft vs Sarasota actives
$645 vs $303
Days on market
16 vs 67 typical
Where $645/sqft sits among the 400 Sarasota actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Sarasota Beach
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Sarasota Beach — neighborhood snapshot
Population
1,619
Median age
68
Median income
$118,409
Median home value
$1,237,714
Avg household
2
Households w/ children
87%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$450K → $491K
Sarasota median sold, yr/yr
95.4%
Sale-to-list ratio (12 mo)
179 of 400
Sarasota actives have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 400% above the SARASOTA 34242 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 5376 SHADOW LAWN DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · May ’26$4,490,000
5362 SHADOW LAWN DRIVE · same community
3 bd · 4 ba · 4,294 sqft · $1,046/sqft · 136 DOM
Sold · Jul ’26$1,750,000
951 CONTENTO ST. · same community
3 bd · 3 ba · 2,882 sqft · $607/sqft · 107 DOM
Sold · Jun ’26$2,225,000
819 PARADISE WAY · same community
3 bd · 2.5 ba · 2,505 sqft · $888/sqft · 10 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Angela Rodriguez
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 5376 SHADOW LAWN DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5376 SHADOW LAWN DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Angela's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
5376 SHADOW LAWN DRIVE FAQs
What would the monthly payment be for 5376 SHADOW LAWN DRIVE?+
With 10% down on a 30-year Conventional loan at 7.5%, the all-in payment lands around $17,095/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 5376 SHADOW LAWN DRIVE?+
The most recent tax bill on record (2025) was $11,182. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5376 SHADOW LAWN DRIVE?+
The listing reports pets: Cats OK, Dogs OK, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Sarasota?+
At $2,400,000, this home is listed about 329% above the Sarasota median of $559,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5376 SHADOW LAWN DRIVE?+
Phillippi Shores Elementary School (elementary), Brookside Middle School (middle), Sarasota High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$2,400,000 runs 400% above the SARASOTA 34242 median — but at 3,721 sqft it's also nearly twice the size of the typical Sarasota listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong assigned schools
Phillippi Shores Elementary School, Brookside Middle School, Sarasota High School — Phillippi Shores Elementary School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of WILLIAM RAVEIS - FLORIDA LLC · Josie Cline. MLS #A4707331.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Sarasota homes, in your inbox
Like 5376 SHADOW LAWN DRIVE but not quite? A daily digest of every new listing in Sarasota — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Angela to ping you on any price or status change →


